A Dance With Death: The Gamble
by Ionized Rose
Summary: After the rebuilding of Beacon Academy, teams RWBY and JNPR wind up throwing a small "Welcome Back" party. During said party, a mysterious freshmen shows up and mentions an urban legend about a training grounds for Hunters and Huntresses across Remnant that has two catches: once you enter, you can't come out until it's cleared, and if you "die" in the arena, you can't come back.
1. Fables and Legends

**Shit... Okay, before anyone else reads the rough edit of this chapter I'm replacing it with this one. Sorry for the inconvenience and hopefully this edit is just as good as the rough draft.**

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 _'Do you believe in gods, Mr. Lefrenier? Do you believe in mystical beings that created, and rule over, their own segments of the world? If so, then where are they now..?'_

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June, 2038

"There's an old legend that goes back to about the generation of our parent's time here at Beacon," A young man wearing a pair work boots, dark blue denim pants, and a black hoodie under an equally dark coloured leather coat that extended down to his knees with a grey bandanna that covered his face while the hood covered the rest of his head said as eight other students that had formed a circle around a dimly lit dorm room paid close attention to his story. It was the last week of the semester at Beacon, and teams RWBY and JNPR had decided to throw a small party amongst themselves and a few guests that they had wanted to join in on the fun. Of which, only one actually showed up thus far, so they had decided on swapping stories until more came. "A legend," he continued after a brief pause to take a sip from his soda, "about how the Headmaster and the team he lead came to be, and how they were brutally torn from this realm of existence..." His voice was calm, but the way he told the story made it seem like he was there to experience the events firsthand.

"This should be good," Yang stated absentmindedly, twirling a lock of her blond mane around one of her fingers.

"Wait, Jon... What do you mean by 'This realm of existence'?" Ruby asked, slightly tilting her head. "Like, they're aliens from another universe or something?"

"Not exactly," Jon replied, thinking on how to phrase his next few sentences so that everyone would understand. "It's more like they found a wormhole to another universe in a way, or so the story goes."

"Bor-ring!" The ever hyper Nora blurted out. "Get to the part with all the action and fighting and stuff!"

Chuckling, Jon raised his hands saying "Fine, if I must. Long story short on one of their missions, team JONS, Ozpin's team, were tasked with storming this abandoned hospital sweep & clear style, but wound up one of their team members, while another died going after the first... Only Ozpin and someone by the name of James got out, haunted by what they saw..."

"Well, that's not dark at all!" Jaune said sarcastically before getting an elbow to the side from Pyrrha that shut him up.

"But..." Jon continued, ignoring the blond leader's comment. "Rumor has it that someone tried bombing this place not too long ago, with enough explosives to level a city block, but when the dust cleared, the building was unscathed and the bomber was found walking in the deserts of Vacuo totally drenched in blood." Weiss gagged at the thought, the others showed their thoughts on their faces from disgust to a mild interest in what might have happened.

Blake set her book to the side, sighing. "That rumor is true..." she began, the angst of her thoughts hung on every word. "The White Fang use to use that hospital as a training grounds for only the toughest of their combatants, but it was more so used to eliminate traitors and those that turned on the rest of their faction for any reason..."

"You know of it?" Jon asked, wanting to confirm a suspicion that arose from her description of the facility in question.

"During my time with them, I managed to clear it a few times," the Ravenette admitted, lowering her head as a shiver overwhelmed her. "But it's only thanks to someone that haunts that place that I'm still alive..."

Nodding understandingly, he sighed, deciding to finish the story. "Apparently, and correct me if I'm wrong Blake, the reward at the end of it is that you have some sort of gift bestowed upon you as well as you can keep everything you're carrying: lien, ammo, weapons, armour..." Looking to Blake, she nodded, her amber eyes glossed over with tears as she was pulled into a hug from the blond brawler beside her. "But if one does enter this place, time outside of it pauses and warps around them so if they make it out alive, it's like nothing ever happened." Again, another nod. "But the wormhole factor of this whole thing is that apparently if you clear this place in a fast enough time, you can travel time or something like it."

A silence fell over the room that was almost deafening, until a wolves howl emitted through the open window that made all of the students jump.

October

Jon was standing in front of the door leading to team RWBY's room…

But he was nervous about asking one of its occupants to the party that one of the Clans, multiple teams that had joined together to form one formal company, had told him about. The only conditions were that you had to bring your own drink (of which he went and got a 2-4 of whisky and rum,) you had to be in costume, and you had to bring someone with you, due to previous parties going astray and a lot of expensive things were damaged and enough idiots would be drunk that night and the plus one would need to drag the other back to their dorm.

'Relax, Jonathan…' he thought as he took a deep breath to calm his nerves 'The worst that could happen is that she denies your invite… right..?'

Raising a balled fist to the door in front of him to knock, the door suddenly swings open and a very pissed off Ruby Rose steps out with her back turned to him, screaming "Like fucking hell I'm going as that two-bit, trashy whore!"

"But Ruby-" Yang tries to but in, but is stopped by Ruby's rant continuing where it left off at.

"No! And that's final!" The Crimson leader yells before slamming the door shut, and sliding down the wall to the left of it.

She was dressed in a black and grey with red highlights coat with a matching colour scheme for her skirt and knee length boots. Her trademark red cloak pinned to her collar, and Crescent Rose slung over her right shoulder. A secondary weapon that Jon had only seen once as nothing but scrap parts on a table her with slung over her left he assumed was the finished work of her latest weapon: a sniper/great axe that, to his knowledge, didn't have a name. To top the outfit off, she dyed her now mid-bicep length hair in the same colour as her cloak.

"There's no way I'm wearing a full leather suit strapped with knives to this party…" she mumbled to herself, oblivious to her audience. "Even if he'd find it 'sexy' or if it 'upped my odds' with him... It's unethical and unnecessary."

Deciding he had heard enough, Jon leaned up against the opposite wall, saying "You never know..."

Looking up quizzically, a blush to rival her cloak crawled up from her neck as she stammered "H-How long have you been there!? How much did you hear!?"

Chuckling lightly, he sat down beside her, raising a knee in front of his chest, allowing the other to fall beside him as he crossed his arms and rested them on his erect leg. "Well… everything after you opened your door and yelled at your sister."

"Half sister" she corrected, causing a puzzled look to cross Jonathan's face, an equally confused stair followed as they maid eye contact. "Different mothers, but the same dad." She explained while looking away.

"I see." he responded in a light monotone.

A moment of silence followed before he broke it off.

"You going to that Halloween party tonight?" He asked, adjusting his glasses.

"It's a couples party, Jay," she said, sadness edging its way into her voice. "That and I'm still single..."

"You really want to go to this party, right?" he asked, looking towards the crimsonette leader, hoping to catch a glance of her silver eyes.

"More than anything…" she whispered, tilting her head towards the ceiling and resting her head on the wall behind her with a light _thud_.

"Even cookies..?" he asked, not anticipating the open palm moving towards his face that ended with a loud _SMACK,_ and Ruby pouting beside him adorably. "Ow! Damn, I was kidding!" chuckling, he rubbed his now reddened cheek.

Sighing, Jonathan considered his next words carefully, before blurting them out. "Ruby..." he practically whispered, not bothering to hide his desperation any further, looking directly ahead of him.

"Yeah..?" She asked, curiosity now leaking into her voice.

"Remember that time we first met?" he asked, rewarding him with a quizzical look again, but he continued anyway. "I figured at that time that you would never notice a nobody like me in Goodwitch's class, and even if you did, you'd never return the feelings I had for you..." he confessed, not caring what happened during it all; he had taken a fancy to the young Reaper at the beginning of the semester the year before, never having the nerve to say anything to her directly and playing the awkward idiot for the longest time.

Still confused, she said "Jay... What exactly are you trying to say?"

A heavy sigh left the young man, giving him a moment to revaluate his confession. After what might have been the longest moment in history, he said "Say if I go as your date…"

"Jay-"

"And this being possibly the first of many…" he interrupted, wanting to get as much of what he needed to say in that moment through to her.

The confusion that had just masked her face melted away to realization and anticipation. "Jay, are you..." is all that she managed as her voice trailed off, hoping that what she thought was happening actually was.

"Yup." he said coolly, anticipating her question.

"You know that-"

"Don't care about the numbers between us." he replied flatly, the corner of his lip twitching upwards a little.

"You relies that-"

"Ruby…" he said looking into her silver eyes for a moment before responding, "Dose it look like I give a fuck what others think about me? Primarily my relationship status?"

A moment passed as she thought about his question and giggled. "Good point."

"Soo…?" he asked, anticipation filling his voice.

"Race you there?" she asked, standing up and straightening her dress.

"No use of semblances!"

"Wha? Come on! What's the point in it then?" She pouted causing the slightly older man (about a year and a half difference) before running past him down the hall towards the stairwell while he was distracted as her pouting.

Struggling to keep up with her, they both made their way to a quiet wing on Beacon's property. Upon arriving to the Clan's private dorm, they were greeted with light music that could be heard behind the buildings doors and lights flickering behind the windows. The building itself looked as if it hadn't been used in years: shattered windows, boarded up side entrances, and chains locked on the front door, spray painted "Keep out! Death awaits" on it.

"This is it?" Ruby asked, trusting her instincts and drawing her scythe.

"Apparently." he said, activating his weapon, "Shall we?"

After a moment of hesitation, she wordlessly nods, as Jon takes out a key, inserts it into the lock on the door, and removing the chain on it.

Opening the door, a raspy voice asks "What… is the colour… of night…?"

Jon, knowing the answer, says "Sanguine, my brother."

The doors creak open, Ruby keeps both her now drawn weapons in their compacted gun forms on the door as the voice says "Welcome… home…"

"Jay…" a worried Ruby says, activating a flashlight attached to her axe's under barrel that lights the darkened hallway ahead of them, "What the fuck is this place..?"

He activates the flashlight on his shotgun before cocking his weapon, and says "The closest thing we got to Hell by the looks of it..." walking in, he asks, "Remember the story I told your team and JNPR back in June?"

"What about it?" she asks, sticking close to him.

"The place was formally called The Gamble over the summer." he explained. "I think this might be it."

"Fuck sakes" the siper says. "What're we up against?"

A blood curdling screech comes from around the corridor, sending the crimsonette on edge.

"Sounds like we got demons this time... Guess we lucked out-"

The screech rings out again as a humanoid in hospital clothing charges them. Taking aim, he fires a single slug into the creatures head. Hitting true, its head explodes as its corps falls lifelessly to the ground.

"Ruby. I'll need you to trust me with this and cover my six." He stated between shots. "I'll explain later."

"This better be a damn good explanation, Jay!" she yelled, firing at whatever came down the hallway.

After dispatching ten more of the creatures, he rotates the custom drum mag of his shotgun, loading in explosive rounds, and sarcastically said "Maybe I'll just take a stroll instead."

As the hordes came, they where just as fast destroyed. After what seemed like three hours of combat, the bodies evaporated and a faint buzzer ran through the halls, followed be a female voice saying, "Floor one complete. Time: Twenty-one minutes."

"Twenty-one minutes flat? Not bad. Almost a record." Jon said as he reloaded his empty clips. "I suggest you do the same."

Dropping her magazines, she says "You mentioned an explanation before all hell broke lose?"

Sighing, he replied calmly "Yeah... Over the summer, I did some digging on The Gamble when I could between flipping burgers, and managed to find some info leading back to the origins of this whole thing... Apparently this thing moves from one abandoned location to the next and upping it's wave factor with every 'floor' we clear... Seriously, you wont be getting those back if you leave them, load them back up."

Deadpanning, she asks "Aaaaaannnnddd whose idea was this?"

"The Headmaster before Ozpin." he replied, loading what shells he had left into a drum mag.

Loading her empty clips, she thought about what she had just went through, and if she'd ever make it out alive.

Loading a clip into his gun, he turned to her and asked "Ready to go?"

Sighing, she reinserted the clips into her rifles, trained her weapons on him, confusion and fear morphed her face into something close to hysteria. "How exactly did you know what was coming for us before it did?"

"Because this isn't my first time here." He sighed. Looking her in the eye, he wore a mask of sadness and seriousness. Both translated into his voice as he explained, "Like I said before, this place is a gateway between worlds: we enter and train, but time back in our world stops until we finish. Every 'floor', once cleared, is like a enemy free dungeon in an RPG video game: loot is able to be plundered, in this case ammo types, lien and weapons parts will be optimal. Every five or so floors a merchant can be found to buy gear and ammo. Around every ten or fifteen is a 'boss' that we have to kill to proceed. This making sense to you?"

"All but one thing…" she said as she lowered her guns, seething Crescent Rose, but keeping her ax trained on him from the hip, "If this is a training ground, what are we supposed to be training for?"

"Which leads me to the team/clan forming." He continued, not missing a beat "Every two or three floors there'll be a civilian from another world. Only three others have reportedly survived this from our world: me, the Headmaster before Ozpin, and our worlds Beta Testers: Team JONS. Rumor has it Scarlet 'Kill Smith' Mason still reside here. The Headmaster keeps coming back to this Hellhole because he can and will, Kill Smith to bring back a fallen friend, went by .50 or something like it. Anyways, if we can find someone and persuade them to join us, it'll quicken the cleared times per 'floor', and reaping its rewards that much faster."

"What do you mean by 'reaping its rewards'?" She asked, annoyance the only thing in her voice.

Taking off his glasses to clean them, he remains silent until he reapplies them to speak again. "Every minute you don't use per floor is added to a counter, everyone's different for their usage, but the theory behind it remains the same: we can use each minute we save to travel time lengths or add them to a life of our choosing. An example being you can turn back time and visit a long dead relative or even resurrecting them with enough saved time."

"And how many floors do we have to clear before we can go home again?"

"99 and the rest of this one... You sure about this?" he asked with a raised brow?

"Do we have a choice? C'mon, let's get going." she said, walking on ahead of him.

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 **Again, sorry for the wrong chapter. Fair warning: my upload time for chapters is as random as Ruby is fast. If you guys like the rough draft better (for those who read it), either drop a review or fire off a PM to me and I'll see what I can do.**


	2. Items and Trust Issues

**Alright, so the last chapter was pretty all over the place. Hopefully this one is at least decent and keeps the ball rolling. Any who, let's get this going.**

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 _If the truth will set you free, why am I still imprisoned here?_

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"Demons, Witches, Bogart's and... what was the last one again?" Ruby asked, taking notes on what she and Jon had encountered through the first four floors of the "training" arena known as _The Gamble_ on her Scroll.

Along their search of the previous floors, they had found only a few small cashes of ammo, the odd lien card, as well as weapons mods: for Ruby it consisted of a barrel chambered for a 24 gauge shotgun almost seemingly as if it were meant to be equipped with Crescent Rose with the colour scheme and design fitting perfectly. Whereas Jon managed to pick up a switch feeding mechanism to switch between his magazines and under barrel tube of his shotgun.

Currently, the duo were casually walking down a narrow, dimly lit hallway, the handful of torches that burned flickered blood red flames onto the grey stone of the walls. At the end of the hallway was their target: an engraved door that was shaped to look like an eye, painted a shade of red as if the architect wanted it to seem to ooze blood.

"Ab-humans," Jon stated coldly, stopping to load an emptied magazine with what he called "Dragons Breath" shells, his eyes flicking between his ammo belt, the emptied magazine in his hand and the door in front of them. "The spawn of mortals - mainly humans, but some Faunus occasionally - and some form of demon. The ones we were fighting were fathered by the one who goes by The Fiend in this generation."

"Oh, well... good to know, I guess." Ruby commented before going back to her scroll to type the information in before she forgot it. "Any guess as to what's next?" She asked, taking a picture of the door.

"Yeah..." he said, loading the last of the shotgun shells he had into emptied magazines and placing them into pockets on his belt. "But it's not going to be an easy opponent like the previous foes that we've faced thus far..." Before Ruby could press him for more on what he meant, he began walking again, approaching the door and looking it over as if to take in every detail of it only to halt 10 meters in front of it. Signaling for Ruby to stop, he took a knee and inspected a stone tile in front of where his left boot had stopped.

Stopping beside the CQB orientated young man, she peered over his shoulder to see a pentagram - a five pointed star with three circles enclosing it - the colour of blood engraved into the grey and black stone that made the door, the series of letters in the lower right corner read " ** _V - X_** ". Remembering seeing something similar to the images on the stone in front of them as a child, confusion flickered into the young leader's voice as she tried to ask on what it meant, but only managed to stammer out "J-Jay..?"

"It's a spell that forces us into the room and bars us from leaving until the next foe is defeated..." he clarified, catching the confusion, but not fully understanding the tone in her voice. "Load every last bullet into your mags if you haven't." he instructed, running a few fingers over the stone. "If you have extra mags afterwards, then load the shotgun slugs you picked up earlier into them; the barrel you got on the third floor will take both your standard bullets and the shells without damaging it too much. This next area has only 1 enemy and the room is going to be in a close quarters style for a mid-boss, so melee may be needed he-"

Having heard about enough and feeling the blood in her begin to boil, the crimsonette did the first thing to come to mind to shut him up by grabbing the collar of his coat, throwing Jon back a couple of meters down the way they had come from. Mid-flight, a storm of rose petals flooded around Jon, a hand on each shoulder was the only thing he felt before a flying knee nailing him in his core, driving the wind from his lungs. Seconds later after a hard landing on the stone floor, unable to move while trying to regain the breath in his lungs, he felt another weight press against his core and shoulders effectively pinning him to the ground.

Groaning and attempting to regain his breath, figuring that resisting would only end in failure, all he managed to do was open his eyes enough to look into the pools of silver above his own, rimmed in red and tears falling from them to land on his cheeks. The compromising position they were in would have left him blushing and rambling excuses to any who witnessed the situation... but not this time...

This time, he could only stare up in shock as the seemingly timid and innocent girl that he had developed feelings for, as she frantically looked in his eyes for some sort of recognition of what she was thinking. "Ru-" he barely whispered, receiving a hard _SMACK_ that echoed through the hallway.

"No!" She screamed hysterically, shaking violently. "Just what the fuck really is this place!? What do you mean by 'mid-boss'!? _WHO_ _**ARE**_ _YOU Jon!?_ Or is that even your actual name..?"

Taken aback from the young crimsonette's sudden change in attitude in such a short amount of time, Jon tried to explain himself, only to get a backhand to the other cheek. "Ow! My other cheek - _Gahckhaha!_ " He commented before screaming out in pain as the sniper drove her knee into his stomach with even more force.

"You have done _NOTHING_ to explain _ANY_ of this other than that vague explanation back on floor one!" Standing over him, the sniper firmly planted her boot on the young man's chest and pointing her weapons' barrel between his eyes. "I'm sick of going through this Hell hole without as much as a hint of what's going on! Start... Talking..." the last two words being said through gritted teeth. "Or you will never see the light of day again..!"

Eyeing the gun to his head before looking back to match her gaze and sighing, closing his eyes and raising his hands. "Alright..." he grunted after a moment. "But you need to let me up; this is going to be a long story in its own right..." At this, Ruby's face changed from hysteria to confusion and anger. "If you want me to tell you what I know, you'll meet me half way with this, Lil' Red. I know more about you, your friends, and your family than what you think. I even know where Yang's mother is currently and what happened to yours..."

Slamming the barrel of her gun into his head, she was about to pull the trigger, but a thought suddenly came to her. _'What if what he's saying is true?'_ Thinking over what he had said, Ruby thought over her choices. If what Jon said was true, then he may have the resources to not just get her back to Beacon in one piece, but also answer questions that she had been pondering over for years now. But if he were lying just to get some sort of foothold in the situation, then she would be compromising her position in this interrogation and, maybe worse, she'd be putting her life on the line more than what it currently was. And what if everything he would tell her would be a lie? Then another thought occurred to the young Huntress: Jon may be the only thing that's kept her alive this far and shooting him now will only drop her odds of living dramatically.

Choosing to pick the middle ground in the situation, Ruby took her foot off of the young man who she wanted answers from and disengaged her weapons safety, not moving it from his face as he tried to rise to stand along with her. "Talk," she demanded, her tone that of distrust and seriousness usually only granted by the most cynical of strategists much older than she was. "It's your answers that are the only reason you're alive currently."

Choosing not to anger the young redhead further, he instead tried the more reasonable approach with her. "Alright... Considering I don't have much of a choice here, where do you want me to start?" he asked, wiping sweat off of his brow, anticipating where she would lead this questioning. _'Seriously, you idiot?'_ he thought to himself, semi sarcastically. _'That's what you're going to ask after how many times of going through this? You know her answer will be -'_

"The beginning..." Ruby growled through her teeth, not giving him any leeway out of the situation.

Sighing, the young man closed his eyes and thought back to the beginning of his story before asking "Are you sure you want to hear what I have to say?" With the cambering of a bullet, he stated coldly "Alright... But remember this: I gave you a chance to avoid this unneeded pain, Ruby Rose..."

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 **AN: Sorry about the wait, readers, but I've been going through some things that have taken up a lot of my time. Also, with being in an University this year for a Sound Tech. course, I've been trying to balance writing and school work in my free time. But if you made it this far, thank you for reading this! And if you have any suggestions on different enemies that our duo may face/other survivors they may encounter later on, don't be afraid to drop them in the reviews section or in a PM. Who know's? I may just use them.**


	3. Update: Deaths and Hacks

**Hey everyone. Sorry about the lack of content over the last few months, but a lot of shit has happened and almost none of it is pretty.**

 **First, my fiance had committed suicide about a week before Christmas. I'll spare you the details, but keep in mind that they may or may not pop up in future chapters.**

 **Secondly, about the time that I had originally had planed to release the next chapter of A Dance with Death: The Gamble, my computer got hacked, frying the hard drive. Fast forward to about last week with five more hard drives now deemed useless, the WiFi chip on the fritz and the battery lasting 20 minutes (if I'm lucky,) and here we are.**

 **Drama and tech problems aside, the next chapter should be up by the end of the month (hopefully) but only god knows.**


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